2009 Is Already Old News. What’s Next for the Yanks?

So, the Yankees have won the World Series for the 27th time. Hooray! It has been a while. Now that you've had some time to sleep off the celebration, though, it's time to get down to business. It wouldn't be the Yankees if we let one little championship distract us from the real goal: Total Global Domination. One title is never enough. How do they get another one next year? Here's a quick look at the off-season issues the Yankees need to resolve.

What to do with Johnny Damon?

As the Game 4 win proved, Damon's a nice fellow to have around when you need someone to do oddly genius sprints around the bases, and his flip-slap left-handed swing is perfectly suited for the wind-tunnel/short fence/physics anomaly that is the right-field power alley. That said, he's not exactly the most brilliant left fielder, and his arm strength is roughly comparable to a child skipping a pebble across a pond. This happens to be an excellent year for free-agent left fielders: Matt Holliday and Jason Bay are available to the highest bidder, and the Rays have batted their eyes at suitors asking about Carl Crawford (who does everything Damon does, but better). Damon desperately wants to stay here — "I desperately want to stay here," he has said, so there's a clue — but keeping guys like Damon around past their expiration dates (Damon turns 36 tomorrow) is exactly the type of Overpaying for Aging Big Name move that has caused the Yankees trouble in the past. We'll know about this one sooner rather than later.

Who's the DH?

The Yankees had more designated-hitter types than they knew what to do with this year — Damon, Nick Swisher, Xavier Nady, Eric Hinske — but they had to put them in the field because Hideki Matsui was too gimpy to trot out there anymore. Matsui's a free agent this off-season, and you have to think the Yankees will see him as a luxury they don't necessarily need. (He'd be a perfect fit taking over for Ken Griffey Jr. as DH in Seattle.) Of course, Hideki made that a wee bit more difficult by winning the World Series MVP, though the last person to win the World Series MVP and not return to his team the next season was John Wetteland in 1996. That turned out okay. If the Yanks don't re-sign Matsui but keep everybody else, Joe Girardi can use the DH spot as a roaming half day of rest for overworked regulars like Derek Jeter, Alex Rodriguez, and (specifically) Jorge Posada, even if the Yanks sign a big hitter like Holliday or Bay. Also, it would be a nice place to put the defensively disinclined Swisher, who was often taken out late in playoff games for Brett Gardner. Our only question: If he's DHing, can he still pose and preen for the Bleacher Creatures who chant his name in the first inning?

Anybody else notice that rotation?

As of this second, the Yankees currently have two of their five rotation spots filled: CC Sabathia and A.J. Burnett. Andy Pettitte is a free agent, and while the Yankees would love for him to return and repeat his 194-and-two-thirds innings of this season, he might be too expensive, he might want to retire, and he might not be able to hold up in his age-38 season anyway. Looks like they'll need him, though. The free-agent crop of pitchers is awfully thin this year (unless the Yanks win a bidding war with the Red Sox for Cuban émigré Aroldis Chapman). Chien-Ming Wang is expected to be back close to healthy, but he's hardly reliable at this point in his career. Then there is Joba Chamberlain and Phil Hughes. If all had gone to plan — which it never does, of course — they'd both be rotation mainstays at this point. It's still a good plan: Talented young arms like theirs shouldn't go to waste pitching three innings a week. But can you possibly count on those guys to pitch every four days? Have we officially decided that's the right use for them? Will they freak out and lose mph's off their fastball again? Joba and (to a lesser extent) Hughes have been among the Yankees' few plans that haven't gone perfectly the last two seasons. What direction the team goes with them will dictate what happens with the highly unsettled rotation.

Psst: Derek Jeter's a free agent after next season. Somebody gonna take care of that?

Lord, it has been forever since Derek Jeter signed that ten-year, $189 million contract. No one remembers now, but the contract negotiations for that deal, signed February 9, 2001, were fairly contentious, and George Steinbrenner, back when he was still George, was piqued enough by the contract that he had his dumb he's-partying-too-much feud with Jeter the very next year.

Well, that contract is up after next season. (It's the most expensive year on the contract, a $22.6 million hit.) You'd have a hard time arguing the Yankees didn't get their money's worth. Before this season, some — including us, and perhaps even mostly us — saw Jeter as a declining player whose name meant more these days than his game. Then he went out and had one of the best years of his career. Still: In the next deal, Jeter will be 36 rather than 26. It's impossible to imagine Jeter playing anywhere else, but it would behoove the Yankees to take care of Jeter before the season begins, lest the contract situation become an issue all year. But for how much? Or, more to the point, how long? Can you sign Jeter for, say, five years, making him 41 years old at the end of the contract? Will he really be able to play shortstop at 41? How few years will Jeter settle for? Even though Jeter surely isn't going anywhere, the negotiations will be delicate. The Yankees have to do what's right for Jeter, but they have to be smart, too.

The time to start thinking about all of this is now. Okay, maybe after the parade.